I Went from “How To” to “What To”
The Good Part of Getting Old
Photo by Kampus Production
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Introduction
Your approach to leadership is shaped by your early experiences.
My first sales job? Selling Girl Scout cookies door-to-door. I sold 258 boxes in two weeks, raising money for my high school band’s NYC festival trip. It didn’t feel like a big deal, but it shaped my approach to cold-calling. Years later, at Fidelis Security, I made 850 cold calls in three months, generating over $650K in sales.
But leadership came later.
My first programming job after graduate school was at Wilshire Associates in Santa Monica. My boss gave me a book on capital markets theory and told me what he wanted to achieve—no hand-holding, just trust.
When we returned to Israel, I joined an application software group in a defense electronics company.
The team leaders, all ex-Army, had no-nonsense views on managing projects and writing code.
That’s where my vision of leadership began.
Define Your Vision Early
After the defense electronics company, we moved to a commune. We were idealists.
At the commune, I led a small software team. Selling our services required learning sales from scratch. I rode buses to the Hebrew University business school library, read books on sales, and came back with this amazing insight: “People buy to satisfy their needs.”
I developed a clear leadership vision for myself: I lead commando teams (programmers) into enemy territory (customers), execute a successful mission (high quality software on time), and bring the team home safely (make a profit).
My leadership vision was not to become CEO of a big tech company.
But leadership isn’t just vision—it’s learning.
Bootstrapping Leadership
After the commune, I went to work for Intel.
At Intel JER3, I sat around the corner from Dov Frohman. If I had a question, I could knock on the side of his cubicle and bounce my idea off him.
Dov once said that leadership cannot be taught but it can be learned.
At Intel, I learned three essential tools for learning leadership.
1. Invisible Mentors
Mentors like Chris Marshall taught me accountability. To this day, I hear his voice: “You’ll pay for that delay in your review.”
2. Reflection
Structured debriefs after every success, failure, and near-miss help me evaluate what worked and what needed to change.
3. Learning from your people
Humility is key. I learned to challenge authority and think outside the box from one of the engineers on my telecom team at Intel.
Bootstrapping Your Next-Generation Self at 53
By 53, I was the co-founder and CTO of a fintech startup. But I was DUI—Driving under the influence of Intel.
I had lost sight of my passion: leading small, high-performance teams.
After two years, the startup failed. I was forced to reflect and restart.
Here’s the truth: People remember your failures, not your successes.
Restore Your Passion
AI lets you automate repetitive tasks—compliance audits, hiring, product launches—so you can focus on what to do, not how to do it.
During an Agentic AI course, I delivered 35 releases in 19 days, despite never writing Python before. Why? I knew what to do and iterated quickly with AI’s help.
You can do the same in biotech or software engineering.
AI is reshaping industries. It’s cutting drug molecule development timelines in half but sidelining researchers who don’t adapt. GenAI is streamlining engineering workflows while companies favor younger, cheaper hires.
Your Expertise, Your Independence
You've got 20+ years of impact ahead.
Why spend them defending your value to executives who see you as another process to optimize?
Your expertise is the cornerstone of your independence. With the right tools and mindset, the next 20 years could be your most impactful yet.
Take 15 minutes today to reflect: What's one skill or piece of expertise you've mastered that AI can't replicate?
Write it down. It might be the key to your next chapter.
I'd love to hear your thoughts and share experiences.
Reply to this email or send me a note on substack if this resonates with you.
Have a great Friday!